F. Badali, W. Issa, Brett R. Pool
Mar 1, 1999
Citations
0
Influential Citations
2
Citations
Journal
Journal of Organometallic Chemistry
Abstract
Abstract Allyltrimethylsilane oxide 5 undergoes regiospecific ring-opening with carboxylic acids in chloroform to give the hydroxy esters 6a – e . In polar solvents competing elimination results in the formation of allyl alcohol. Allyltriisopropylsilane oxide 17 undergoes analogous reactions as 5 in chloroform but does not undergo elimination in methanol or acetone. The X-ray structures of 18b and 18c reveal significant lengthening of the C–O (ester) bond (a remarkable 1.502(2) A for 18c ), these structural effects are due to strong σ C–Si – σ * C–O interactions, particularly for 18c .